3-acetamido-N-(2-mercaptoethyl) propanamide | 31645-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-acetamido-N-(2-mercaptoethyl) propanamide
• 英文别名: 3-acetamido-N-(2-mercaptoethyl)propanamide；N-acetyl β-aletheine；N-(N-acetyl-beta-alanyl)cysteamine；3-acetamido-N-(2-sulfanylethyl)propanamide
• CAS: 31645-52-0
• 化学式: C₇H₁₄N₂O₂S
• 分子量: 190.266
• InChiKey: UTUANHHJYGDYCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetamido-N-(2-mercaptoethyl) propanamide 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 N¹-<2-(S,N-acetyl β-aletheinyl) acetyl> spermidine amide dihydrochloride
  参考文献：
  名称：

  Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.

  摘要：

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.

  DOI：

  10.1016/s0040-4020(01)80153-8
• 作为产物：
  描述：

  N,N'-diacetyl-β-alethine 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以92%的产率得到3-acetamido-N-(2-mercaptoethyl) propanamide
  参考文献：
  名称：

  Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.

  摘要：

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.

  DOI：

  10.1016/s0040-4020(01)80153-8

文献信息

• Design, synthesis and in vitro antikinetoplastid evaluation of N-acylated putrescine, spermidine and spermine derivatives
  作者：Elodie Jagu、Rachid Djilali、Sébastien Pomel、Florence Ramiandrasoa、Stéphanie Pethe、Raphaël Labruère、Philippe M. Loiseau、Casimir Blonski

  DOI：10.1016/j.bmcl.2014.11.073

  日期：2015.1

  structure–activity relationship study on polyamine derivatives led to the synthesis and the determination of antikinetoplastid activity of 17 compounds. Among them, a spermidine derivative (compound 13) was specifically active in vitro against Leishmania donovani axenic amastigotes (IC50 at 5.4 μM; Selectivity Index >18.5) and a spermine derivative (compound 28) specifically active against Trypanosoma

  对多胺衍生物的构效关系研究导致了17种化合物的合成和抗运动型活性的测定。其中，亚精胺衍生物（化合物13）在体外对利什曼原虫多虫尼阿米虫（IC 50为5.4μM ；选择性指数> 18.5）具有特异性活性，而亚精胺衍生物（化合物28）对布氏锥虫（Trypanosoma brucei gambiense）具有特异性活性（IC 50对1.9μM;选择性指数> 52）。
• Postsynthetic Modification of Bacterial Peptidoglycan Using Bioorthogonal <i>N</i>-Acetylcysteamine Analogs and Peptidoglycan <i>O</i>-Acetyltransferase B
  作者：Yiben Wang、Klare M. Lazor、Kristen E. DeMeester、Hai Liang、Tyler K. Heiss、Catherine L. Grimes

  DOI：10.1021/jacs.7b06820

  日期：2017.10.4

  Bacteria have the natural ability to install protective postsynthetic modifications onto its bacterial peptidoglycan (PG), the coat woven into bacterial cell wall. Peptidoglycan O-acetyltransferase B (PatB) catalyzes the O-acetylation of PG in Gram (-) bacteria, which aids in bacterial survival, as it prevents autolysins such as lysozyme from cleaving the PG. We explored the mechanistic derails of PatB's acetylation function and determined that PatB has substrate specificity for bioorthgonal short N-acetyl cysteamine (SNAc) donors. A variety of functionality including azides and alkynes were installed on tri-N-acetylglucosamine (NAG)3, a PG mimic, as well as PG isolated from various Gram (+) and Gram () bacterial species. The bioorthogonal modifications protect the isolated PG against lysozyme degradation in vitro. We further demonstrate that this postsynthetic Modification of PG can be extended to use click chemistry to fluorescently label the mature PG in whole bacterial cells of Bacillus subtilis. Modifying PG postsynthetically can aid in the development of antibiotics and immune modulators by expanding the understanding of how PG is processed by lytic enzymes.
• PARELLO, JOSEPH;ROBLOT, GEORGES;WYLDE, RENEE;MARTIN, AIMEE, C. R. ACAD. SCI. SER. 2, 310,(1990) N1, C. 1441-1446
  作者：PARELLO, JOSEPH、ROBLOT, GEORGES、WYLDE, RENEE、MARTIN, AIMEE

  DOI：——

  日期：——
• Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.
  作者：Georges Roblot、Renée Wylde、Aimée Martin、Joseph Parello

  DOI：10.1016/s0040-4020(01)80153-8

  日期：1993.1

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.